diff --git a/ui/src/components/contextual-sidebar-styles.test.ts b/ui/src/components/contextual-sidebar-styles.test.ts
new file mode 100644
index 00000000000..10c5ddf2c4e
--- /dev/null
+++ b/ui/src/components/contextual-sidebar-styles.test.ts
@@ -0,0 +1,16 @@
+import { describe, expect, it } from "vitest";
+import { contextualSidebarStyles } from "./contextual-sidebar-styles";
+
+describe("contextualSidebarStyles.section", () => {
+  it("separates later sections with a margin and a top border", () => {
+    const classes = contextualSidebarStyles.section.split(" ");
+    expect(classes).toContain("mt-4");
+    expect(classes).toContain("border-t");
+  });
+
+  it("removes the margin and border from the first section", () => {
+    const classes = contextualSidebarStyles.section.split(" ");
+    expect(classes).toContain("first:mt-0");
+    expect(classes).toContain("first:border-t-0");
+  });
+});
diff --git a/ui/src/components/contextual-sidebar-styles.ts b/ui/src/components/contextual-sidebar-styles.ts
index 3b05540f597..a88989b7f6d 100644
--- a/ui/src/components/contextual-sidebar-styles.ts
+++ b/ui/src/components/contextual-sidebar-styles.ts
@@ -7,7 +7,7 @@
 export const contextualSidebarStyles = {
   nav: "flex min-h-0 flex-1 flex-col overflow-y-auto scrollbar-auto-hide px-3 py-2",
   group: "flex flex-col gap-0.5",
-  section: "mt-4 border-t border-border pt-3",
+  section: "mt-4 border-t border-border pt-3 first:mt-0 first:border-t-0",
   sectionLabel:
     "px-2 pb-1 text-(length:--text-micro) font-semibold uppercase tracking-wide text-muted-foreground",
   sectionDescription: